Synthesis, Surface-Active Properties, and Anthelmintic Activities of New Cationic Gemini Surfactants Against the Gastrointestinal Nematode, Heligmosomoides polygyrus bakeri, in vitro

V.G. SÁNCHEZ, C.J. GIUDICI, A.R. BASSI AND M.C. MURGUÍA

JOURNAL OF SURFACTANTS AND DETERGENTS

SPRINGER HEIDELBERG

Lugar: Heidelberg; Año: 2012 vol. 15 p. 463 - 470

1097-3958

A novel series of cationic dimeric surfactants were prepared involving ketalization reaction, Williamson etherification, and regioselective oxirane ring opening with tertiary alkyl amines. The synthesized compounds were obtained in high purity by a simple purification procedure on column chromatography. The critical micelle concentration (CMC), effectiveness of surface tension reduction (gCMC), surface excess concentration (G), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation properties. For the first time, we reported the anthelmintic activities against the rodent gastrointestinal nematode Heligmosomoides polygyrus bakeri, in vitro for cationic gemini compounds. In the series of five tested cationic compounds (4a-e), three of them (4a, 4b and 4d) were shown to have an excellent anthelmintic activity in vitro at different concentrations. The anthelmintic activity was found to be dependent from the type of cationic compound, concentration and incubation time. The cationic di-C12 (4a) derivate of the series was the best anthelmintic agent, optimizing its use to a minimum concentration of 50 ppm and 60 minutes of incubation.